CN1109040C - Alkylene-bridged alkyl phosphonates - Google Patents

Alkylene-bridged alkyl phosphonates Download PDF

Info

Publication number
CN1109040C
CN1109040C CN97114159A CN97114159A CN1109040C CN 1109040 C CN1109040 C CN 1109040C CN 97114159 A CN97114159 A CN 97114159A CN 97114159 A CN97114159 A CN 97114159A CN 1109040 C CN1109040 C CN 1109040C
Authority
CN
China
Prior art keywords
acid ester
phosphonic acid
formula
alkyl
fire retardant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CN97114159A
Other languages
Chinese (zh)
Other versions
CN1183416A (en
Inventor
C·J·哈里斯
G·乌瓦尔德
A·J·泰勒尔
J·S·曼库
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Albemarle Chemicals UK Ltd
Original Assignee
Rhodia Consumer Specialties Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhodia Consumer Specialties Ltd filed Critical Rhodia Consumer Specialties Ltd
Publication of CN1183416A publication Critical patent/CN1183416A/en
Application granted granted Critical
Publication of CN1109040C publication Critical patent/CN1109040C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4075—Esters with hydroxyalkyl compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
    • C08G79/025—Polyphosphazenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Fireproofing Substances (AREA)
  • Paints Or Removers (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Halogen-free, oligomeric or polymeric, alkylene-bridged alkyl phosphonates having the general formula, where n is a whole number of from 1 to 20; R1 and R5 are each C1-C6 alkyl; R2 and R4 are each C2-C10 alkyl and R3 is C2-C10 alkyl. The use of such phosphonates as, or in connection with, a flame-retardant (e.g. for polyurethane foams, resins and composites, epoxy resins, phenolic resins, paints, varnishes or textiles).

Description

Alkylene-bridged alkyl phosphonates
The present invention relates to alkylene-bridged alkyl phosphonates, relate to special we and believe it is new phosphonic acid ester, relate to this phosphonate and use as fire retardant or with the fire retardant bonded and relate to the goods that its fire retardant is made.
For safety, fire retardant is added in a lot of products, so that suppress flame spreading by product.Fire retardant can for example play rapid knock down the flame, or works by making product be difficult to light.When fire retardant is used to handle fiber, soft furniture etc. traditionally, especially joined in foam, coating and the resin such as Resins, epoxy, among much other application is being developed at present energetically, particularly in electronics, automobile, space flight and industrial components.
Polyurethane foam is widely used for various types of chair components, especially the chair component of automobile.These polyurethane foams are not inherent fire retardants (products of combustion of in fact a lot of polyurethane foams has severe toxicity) thereby need to add certain flame retardance element.
Have been found that traditional a lot of fire retardants that are used in combination with the polyurethane foam chair component have along with time-shift and/or evaporable trend.This trend is unfavorable especially for the situation of the polyurethane foam member of automotive seat, and the migration of fire retardant and/or volatilization cause the glass surface " knot mist " such as window or panel board in automobile.
In addition, using halogen-containing phosphonic acid ester is undesirable as fire retardant based on the reason of environment.
We find some not oligopolymer or polymkeric substance of the alkyl phosphonates of halogen-containing alkylidene group-bridge joint, give polyurethane foam especially with gratifying flame-retarding characteristic.In addition, these phosphonic acid esters have shown when foam and have greatly reduced " knot mist " when the automotive seat member.
Thus, the present invention relates to the oligopolymer or the polymkeric substance of the alkyl phosphonates of not halogen-containing alkylidene group-bridge joint that (I) structure that has general formula is provided:
Figure C9711415900051
In the formula:
N is 1～20 integer;
R 1And R 5Each is the alkyl that 1～6 carbon atom is arranged for (they can be identical or different);
R 2And R 4Each is the alkyl that 2～10 carbon atoms are arranged for (they can be identical or different); And
R 3It has been the alkyl that 2～10 carbon atoms are arranged of " alkylidene group-bridge joint " group effect.
The present invention also provides the phosphonic acid ester as the aforesaid general formula of having of a kind of new compound (I) structure, wherein:
The mean value of n is 3;
R 1And R 5Each is a methyl;
R 2And R 4Each is a butyl; With
R 3It is hexyl.
The present invention also provides the phosphonic acid ester as the aforesaid general formula of having of a kind of new compound (I) structure, wherein:
The mean value of n is 6;
R 1And R 5Each is a methyl;
R 2And R 4Each is a butyl; With
R 3It is hexylidene.
The present invention provides the phosphonic acid ester as the aforesaid general formula of having of a kind of new compound (I) structure again, wherein:
The mean value of n is 3;
R 1And R 5Each is an ethyl;
R 2And R 4Each is a butyl;
R 3It is hexyl.
The present invention also provides the application as the phosphonic acid ester of the aforesaid general formula of having of fire retardant (I) structure.
At last, the invention provides by use and have the goods that the fire retardant of the phosphonic acid ester of aforesaid general formula (I) structure is made.
With regard to the phosphonic acid ester with general formula (I) structure, following variation can be within the scope of the invention so.
N can be 3～8 integer of (for example 3),
R 1And R 5Each can be methyl or ethyl;
R 2And R 4Each is that 3～8 carbon atoms, the alkyl of 4～6 carbon atoms are for example arranged, as R 2And R 4Each is a butyl.
R 34～8 carbon atoms can be arranged and can for example be hexyl.
R 3Can be straight or branched, can contain some substituting group for example oxygen or nitrogen in addition.
As with regard to the use of fire retardant, this use comprises to be provided for foam, particularly the flame retardant resistance of polyurethane foam with regard to phosphonic acid ester according to the present invention.Especially, phosphonic acid ester according to the present invention has found the special application that is used for the goods made by polyurethane foam as fire retardant, and for example as the automotive seat member, the there requires to have the character of " low-the knot mist ".
Use according to other of phosphonic acid ester of the present invention, be included in the fire retardant of epoxy resin, polyurethane resin and composition, resol, coating, varnish and fabric, or with they bonded fire retardants.
" phosphonic acid ester " component of the oligopolymer of phosphonic acid ester of the present invention or polymkeric substance is from phosphoric acid (H 3PO 3) or from the conventional deutero-of its alkyl or aryl derivative.
The present invention will specify by following examples:
The common process of preparation alkyl phosphonates oligopolymer
1, (Z+1) part dialkyl phosphite and Z part polyvalent alcohol are mixed in the presence of the suitable transesterification catalyst (for example sodium methylate) of 0～10 mole of % (preferred 0.1～2.0 mole of %) and heat at 50～200 ℃, in order to the H-phosphonate oligomers of formation element length=Z.When distillation, be recovered to the unitary alkyl alcohol of 2Z.The alcohol of actual recovered will depend on used phosphonous acid dialkyl.
2, with H-phosphonate oligomers under the free radical addition condition (for example 140 ℃; 1～2 mole of % ditertiary butyl peroxide is as free-radical initiator) handle with (Z+1) part unsaturated (preferred α-unsaturated) hydrocarbon (for example alkene or alkynes), and can be randomly, in the situation of gaseous state unsaturated hydrocarbons be higher than and (promptly under pressure, react) processing under the atmospheric condition.
3, will generate a kind of rough high acid value alkyl phosphonates oligopolymer like this, then it is handled with a kind of appropriate means/reagent (for example propylene oxide) so that acid number is reduced to proper level and be used for using (for example as the fire retardant of polyurethane foam, the acid number of this moment should be no more than 1.0 milligrams of KOH/g.cpd).
4, product is carried with vacuum gas so that remove residual volatile matter, reclaims pure product.
Embodiment 1
Preparation phosphonic acids butyl ester, dimethyl ester oligopolymer, n=6.10 profiles are suitable for the distillatory reactor, the dimethylphosphite of packing into (770 grams; 7 moles), hexane-1, the 6-glycol (708 the gram; 6 moles) and (0.035 mole of sodium methylate; 7.6 restrain 25% methanol solution).2) reaction mixture of Jiao Baning is heated to 90 ℃, begins to occur at this temperature distillate.Further be heated to 125 ℃ of formation of collecting 330 gram distillates and causing phosphonic acids hydrogen ester oligopolymer.3) Zhuan Zhi profile is readjusted to be suitable for backflow and to be heated to 135 ℃.During 10 hours, butylene and part ditertiary butyl peroxide (15 are restrained altogether then; 1.5 mole %) be added in the reaction mixture together.4) after this, mixture is cooled to room temperature in order to stay crude product, and the acid number of this product is 8.3 milligrams of KOH/g.cpd.5) propylene oxide (70 gram) is added in the crude mixture in during 3 hours at 110 ℃, then 110 ℃ with this mixture reheat 1 hour, be cooled to room temperature then.6) reaction mixture vacuum gas is carried (20mmHg; 20～110 ℃; 1 hour) stay the product (1210 gram) of thick liquid, its acid number is 0.11 milligram of KOH/g.cpd, theoretical phosphorus content is 14.6%.
Embodiment 2
Phosphonic acids butyl ester, the diethyl ester oligopolymer 1 of preparation hexylidene-bridge joint) profile is suitable for the distillatory reactor, packs 1 into, 6-hexylene glycol (354 grams; 3 moles), fusion in inert atmosphere then.2), add diethyl phosphite (DEHP) (552 grams subsequently toward in this molten mixture of 60 ℃ of heating and stirring, adding tetra-sodium methyl esters (MAPP) as catalyzer (3); 4 moles).3) under agitation this mixture slowly is heated to 135 ℃, under this temperature, begins to collect distillate.In then during 3 hours this mixture is heated to 150 ℃ from 135 ℃, further collects distillate during this period.Then with mixture 150 ℃ of reheat 1 hour, during this period nitrogen-blow is led in this reaction mixture.During heating collect the distillate (mainly containing ethanol) of total amount 258 grams.4) mixture is cooled to 140 ℃, the modifier profile makes and is suitable for refluxing.During 15 hours butylene is added in the mixture (12 grams altogether with the part ditertiary butyl peroxide; 2 moles of %w.r.tDEHP).5) after this, mixture is cooled to room temperature in order to stay crude product, and the acid number of this product is 16.5 milligrams of KOH/g.cpd.6) with this crude mixture 110 ℃ of heating.In 3 hours, add propylene oxide (60 gram).This mixture is cooled to room temperature then 110 ℃ of reheat 1 hour.7) reaction mixture vacuum gas is carried (20mmHg; 20～110 ℃; 1 hour) stay heavy-gravity, lurid product liquid (844 gram), its acid number is 0.6 milligram of KOH/g.cpd, theoretical phosphorus content is 14.5%.
Embodiment 3
Hexylidene-bridge joint the oligopolymer 1 of preparation phosphonic acids butyl ester, dimethyl ester) profile is suitable for the distillatory reactor, packs 1 into, 6-hexylene glycol (354 grams; 3 moles), in inert atmosphere, melt then.2), add dimethylphosphite (DMHP) (440 grams subsequently toward in this molten mixture of 60 ℃ of heating and stirring, adding tetra-sodium methyl esters (MAPP) as catalyzer (3); 4 moles).3) under agitation this mixture slowly is heated to 125 ℃, under this temperature, begins to collect distillate.In then during 3 hours this mixture is heated to 150 ℃ from 125 ℃, collects more distillate during this period.Then with mixture 150 ℃ of reheat 1 hour, during this period nitrogen-blow is led in this reaction mixture.During heating collect the distillate (mainly containing methyl alcohol) of total amount 168 grams.4) mixture is cooled to 140 ℃, the modifier profile makes and is suitable for refluxing.During 15 hours butylene is added in the mixture (12 grams altogether with the part ditertiary butyl peroxide; 2 moles of %w.r.t.DMHP).5) after this, mixture is cooled to room temperature in order to stay crude product, and the acid number of this product is 29.6 milligrams of KOH/g.cpd.6) with this crude mixture 110 ℃ of heating.In 3 hours, add propylene oxide (50 gram).This mixture is cooled to room temperature then 110 ℃ of reheat 1 hour.7) reaction mixture vacuum gas is carried (20mmHg; 20～110 ℃; 1 hour) stay heavy-gravity, lurid product liquid (823 gram), its acid number is 1.1 milligrams of KOH/g.cpd, theoretical phosphorus content is 15.0%.
Embodiment 4
Use a kind of traditional halogenation alkyl phosphonates and the product of embodiment 1 (above-mentioned), every kind of preparation that is used for polyurethane foam as flame-retardant additive.Its consumption and the results are shown in (following) in the Table I that obtains.
Table I
Polyester form contrast of the present invention
Prescription phosphonate ester phosphate PPG umber 100.00 100.00 (OH value=8) moisture content several 4.15 4.15 (a) catalyst I umbers 0.04 0.04 (b) catalyst I I umbers 0.12 0.12 (c) surfactant umber 1.30 1.30 stannous octoate umbers 0.25 0.25 toluene diisocyanate index 110 110 (d) phosphonic acids umber of the present invention 10.00-ester (e) tester phosphate umber-13.00 is density kg/m seconds 105.00 111.00 time that swells second 19.00 20.00 creamy time323.60 26.20 Federal Motor Vehicle Safety Standards, 302 performance index burning length mm--combustion time second--speed oneself extinguishes the index knot mist performance knot mist milligram/10 millimeters foams 0.45 1.18 that oneself extinguish DIN75201 B part
A kind of amine catalyst of the explanation of table 1 (a) contains 70% pair of (2-dimethyl aminoethyl) ether and 30% dipropylene glycol, with NIAX *Al buys.(b) a kind of amine catalyst contains 33% 2-aza-bicyclo-octane and 67% dipropylene glycol, with DABCO *33LV buys.(c) a kind of polyether-modified polysiloxane is with TEGOSTAB *BF2370 buys.(d) product of embodiment 1, i.e. phosphonic acids butyl ester (dimethyl ester) oligopolymer of hexylidene-bridge joint.(e) a kind of chlorating alkyl phosphate is with AMGARD *V6 buys. *NIAX, DABCO, TEGOSTAB and AMGARD are registered trademarks.

Claims (22)

1, the oligopolymer or the polymkeric substance that have the not halogen-containing alkylene-bridged alkyl phosphonates of general formula (I) structure: In the formula:
N is 3～8 integer;
R 1And R 5Each is the alkyl that 1～6 carbon atom is arranged independently;
R 2And R 4Each is the alkyl that 2～10 carbon atoms are arranged independently;
R 3It has been the alkyl that 2～10 carbon atoms are arranged of alkylidene group bridge joint group effect.
2, according to the phosphonic acid ester of claim 1, wherein, in formula (I), the mean value of n is 3.
3, according to the phosphonic acid ester of claim 1, wherein, in formula (I), R 1And R 5Each is a methyl.
4, according to the phosphonic acid ester of claim 1, wherein, in formula (I), R 1And R 5Each is an ethyl.
5, according to the phosphonic acid ester of claim 1, wherein, in formula (I), R 2And R 4Each is the alkyl that 3～8 carbon atoms are arranged independently.
6, according to the phosphonic acid ester of claim 5, wherein, in formula (I), R 2And R 4Each is the alkyl that 4～6 carbon atoms are arranged independently.
7, according to the phosphonic acid ester of claim 5, wherein, in formula (I), R 2And R 4Each is a butyl.
8, according to the phosphonic acid ester of claim 1, wherein, in formula (I), R 3Be that 4～8 carbon atom alkyls are arranged.
9, phosphonic acid ester according to Claim 8, wherein, in formula (I), R 3It is hexylidene.
10, phosphonic acid ester according to Claim 8, wherein, R 3It is straight chained alkyl.
11, phosphonic acid ester according to Claim 8, wherein, R 3It is branched-chain alkyl.
12, according to the phosphonic acid ester of claim 1, wherein, this substituted radical or each substituted radical are oxygen or nitrogen.
13, according to the phosphonic acid ester of claim 1, wherein, in formula (I),
The mean value of n is 3;
R 1And R 5Each is a methyl;
R 2And R 4Each is a butyl; And R 3It is hexylidene.
14, according to the phosphonic acid ester of claim 1, wherein, in formula (I),
The mean value of n is 6;
R 1And R 5Each is a methyl;
R 2And R 4Each is a butyl; And R 3It is hexylidene.
15, according to the phosphonic acid ester of claim 1, wherein, in formula (I),
The mean value of n is 3;
R 1And R 5Each is an ethyl;
R 2And R 4Each is a butyl; And R 3It is hexylidene.
16, use as the application of fire retardant or with the fire retardant bonded according to the phosphonic acid ester of claim 1.
17, according to the fire retardant of claim 16 in polyurethane foam application or use with the polyurethane foam bonded.
18, use according to the application of fire retardant in epoxy resin, polyurethane resin, polyurethane composition, resol, coating, varnish and fabric of claim 16, or with their bonded.
19, according to the application of the fire retardant of the phosphonic acid ester with following formula of claim 16:
Figure C9711415900031
In the formula:
n＝3；
R 1And R 5Each is methyl or ethyl;
R 2And R 4Each is a butyl; And R 3It is hexylidene.
20,, wherein will require 1 phosphonic acid ester to be used for the manufacture method of fire retardant goods according to profit according to the application of claim 16.
21, according to the application of claim 20, wherein said goods are to be made by polyurethane foam.
22, according to the goods of claim 20, it is a kind of member of automotive seat.
CN97114159A 1996-11-13 1997-11-13 Alkylene-bridged alkyl phosphonates Expired - Fee Related CN1109040C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9623584.1A GB9623584D0 (en) 1996-11-13 1996-11-13 Alkylene-bridged alkyl phosphonates
GB9623584.1 1996-11-13

Publications (2)

Publication Number Publication Date
CN1183416A CN1183416A (en) 1998-06-03
CN1109040C true CN1109040C (en) 2003-05-21

Family

ID=10802854

Family Applications (1)

Application Number Title Priority Date Filing Date
CN97114159A Expired - Fee Related CN1109040C (en) 1996-11-13 1997-11-13 Alkylene-bridged alkyl phosphonates

Country Status (19)

Country Link
US (1) US6043305A (en)
EP (1) EP0845474B1 (en)
JP (1) JPH10147648A (en)
KR (1) KR19980042404A (en)
CN (1) CN1109040C (en)
AT (1) ATE233776T1 (en)
AU (1) AU721694B2 (en)
CA (1) CA2221079A1 (en)
DE (1) DE69719465T2 (en)
DK (1) DK0845474T3 (en)
ES (1) ES2194161T3 (en)
GB (2) GB9623584D0 (en)
HU (1) HUP9702004A3 (en)
NO (1) NO975194L (en)
NZ (1) NZ329153A (en)
PL (1) PL187503B1 (en)
PT (1) PT845474E (en)
TW (1) TW438851B (en)
ZA (1) ZA9710217B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1022315B1 (en) 1999-01-19 2014-11-12 Poly-Med Inc. Phosphonylated derivatives of aliphatic heterochain and acrylate polymers and applications thereof
EP1031574A1 (en) * 1999-02-26 2000-08-30 Ucb S.A. Phosphorylated polyol, oligomer therefrom, polymer therefrom, processes for preparing them and their uses
KR100355807B1 (en) * 2000-05-17 2002-10-19 박홍수 Modified polyester pre-polymer containing phospate, preparing method thereof, and method for preparing rapid curing type two-component polyurethane flame retardant coatings including the same
EP2166013B1 (en) * 2001-10-04 2018-01-24 Akzo Nobel N.V. Oligomeric, hydroxy-terminated phosphonates
GB0304831D0 (en) * 2003-03-04 2003-04-09 Rhodia Consumer Specialities L Isocyanate adducts
US7067076B2 (en) * 2003-08-01 2006-06-27 Rhodia Inc. Flame retardant phosphonate additives for thermoplastics
JP2005338008A (en) * 2004-05-28 2005-12-08 Asahi Kasei Electronics Co Ltd Testing fixture substrate, test device, and testing method of sensor
EP1885788A2 (en) * 2005-05-27 2008-02-13 Supresta LLC Flame-retardant flexible polyurethane foam
KR100817399B1 (en) * 2005-12-29 2008-03-27 제일모직주식회사 Flameproof thermoplastic Resin Composition
WO2008016632A1 (en) * 2006-08-01 2008-02-07 University Of Massachusetts Deoxybenzoin-based anti-flammable polyphosphonate and poly(arylate-phosphonate) copolymer compounds, compositions and related methods of use
CN102250140A (en) * 2011-05-24 2011-11-23 北京化工大学 Polyphosphinate monomer, polyphosphinate and preparation method of polyphosphinate
KR101783074B1 (en) * 2013-03-12 2017-09-29 (주)엘지하우시스 Envelope including glass fiber for vacuum insulation panel and vacuum insulation panel having the same
US9944879B2 (en) * 2014-10-08 2018-04-17 Afton Chemical Corporation Phosphorous-containing compounds and uses thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3627726A (en) * 1969-01-14 1971-12-14 Textron Inc Polyurethane coatings having intumescent properties
US4092377A (en) * 1974-08-30 1978-05-30 Stauffer Chemical Company Process for preparing polyalkylene glycol alkyl or haloalkyl polyphosphonates
US3978166A (en) * 1975-04-07 1976-08-31 Borg-Warner Corporation Cyclic phosphonates
US4097560A (en) * 1977-06-29 1978-06-27 M & T Chemicals Inc. Novel phosphorus compounds and flame retardant compositions containing same
DE2853936A1 (en) * 1978-12-14 1980-07-03 Bayer Ag PHOSPHONIC ACID ESTER
DE2918672A1 (en) * 1979-05-09 1980-11-20 Hoechst Ag METHOD FOR BRIGHTENING AND COLORING SYNTHESIS FIBERS
DE3007714A1 (en) * 1980-02-29 1981-10-08 Hoechst Ag, 6000 Frankfurt OLIGOMER PHOPHONIC ACID ESTERS AND THE USE THEREOF AS FLAME-RETARDANT
DE3803030C2 (en) * 1988-02-02 1995-04-06 Boehme Chem Fab Kg Use of phosphonates as flame retardants in plastics
TW316907B (en) * 1994-12-28 1997-10-01 Yoshitomi Pharmaceutical
US5919965A (en) * 1995-01-18 1999-07-06 Genzyme Corporation Non-nucleotide phosphorus ester oligomers

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
J.MED,CHEM VOL.9(2) 1966-01-01 *
J.MED,CHEM VOL.9(2) 1966-01-01;ZHUR,OBSHEHEI,KBIM VOL.31 1961-01-01;ZHUR,OBSHEHEI.KBIM VOL.33 1963-01-01 *
ZHUR,OBSHEHEI,KBIM VOL.31 1961-01-01 *
ZHUR,OBSHEHEI.KBIM VOL.33 1963-01-01 *

Also Published As

Publication number Publication date
PL187503B1 (en) 2004-07-30
KR19980042404A (en) 1998-08-17
EP0845474A1 (en) 1998-06-03
AU721694B2 (en) 2000-07-13
ZA9710217B (en) 1998-06-03
JPH10147648A (en) 1998-06-02
NZ329153A (en) 1998-07-28
CA2221079A1 (en) 1998-05-13
GB2319251A (en) 1998-05-20
NO975194D0 (en) 1997-11-12
DE69719465T2 (en) 2003-10-30
ATE233776T1 (en) 2003-03-15
PT845474E (en) 2003-07-31
DE69719465D1 (en) 2003-04-10
GB9623584D0 (en) 1997-01-08
HU9702004D0 (en) 1998-01-28
HUP9702004A2 (en) 1998-07-28
GB2319251B (en) 2000-05-03
ES2194161T3 (en) 2003-11-16
HUP9702004A3 (en) 2000-03-28
NO975194L (en) 1998-05-14
US6043305A (en) 2000-03-28
PL323099A1 (en) 1998-05-25
EP0845474B1 (en) 2003-03-05
GB9722741D0 (en) 1997-12-24
CN1183416A (en) 1998-06-03
DK0845474T3 (en) 2003-07-07
AU4511997A (en) 1998-05-21
TW438851B (en) 2001-06-07

Similar Documents

Publication Publication Date Title
CN1109040C (en) Alkylene-bridged alkyl phosphonates
GB1598215A (en) Preparation of silylorganic esters of phosphorus
JPS6225706B2 (en)
WO2003099919A1 (en) Blends of (alkyl substituted) triaryl phosphate esters with phosphorus-containing flame retardants for polyurethane foams
WO2017193463A1 (en) Composite phosphorus flame retardant comprising cyclic organophosphate with multiple dopo moieties, and manufacturing method thereof
CN104093726A (en) Mixtures of diphosphinic acids and alkylphosphonic acids, process for the preparation thereof and the use thereof
CN112250858A (en) Method for preparing flame-retardant polymer polyol, application and polyurethane foam plastic prepared by using flame-retardant polymer polyol
KR100624629B1 (en) Flame-Retardant Aromatic Polyamide Resin Composition and Molded Object
KR100541629B1 (en) Masses which may be cross-linked to give elastomers with cleavage of alcohols from alkoxysilyl end groups
Levchik et al. Developments in phosphorus flame retardants
US5481014A (en) Silyl phosphonate as stabilizing agent for polydiorganosiloxanes
KR20030082421A (en) Flame retardants for polymers comprising a mixture of two different aryl phosphates, their preparation and their use
JPH09104804A (en) Flame-resistant epoxy resin molding material
US5710300A (en) Siloxy phosphonate as stabilizing agent for polydiorganosiloxanes
US4152371A (en) Copolycondensation products of β-haloalkyl phosphates and dialkyl phosphonates
JP4361937B2 (en) Method for producing organosiloxane modified with phosphonic acid ester
US4086303A (en) Copolycondensation products of β-haloalkyl phosphates and dialkyl phosphonates
EP1210352B1 (en) Formation of oligomeric organophosphorus compositions with improved color
JPH021761A (en) Lithium phosphonate and polymer composition containing it
WO1997044385A1 (en) Flame retardant polyketone composition
CN1074016C (en) Flame-retarded thermosetting resin composition
WO1996011996A1 (en) Viscosity modification of high viscosity flame retardants
US4202842A (en) Copolycondensation products of beta-haloalkyl phosphates and dialkyl phosphonates
US4297138A (en) Copolycondensation products of β-haloalkyl phosphates and dialkyl phosphonates
US4225522A (en) Copolycondensation products of β-haloalkyl phosphates and dialkyl phosphonates

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
ASS Succession or assignment of patent right

Owner name: ALBEMARLE BRITISH CHEMICALS CO., LTD.

Free format text: FORMER OWNER: RHODIA CONSUMPTION SPECIAL CO., LTD.

Effective date: 20040716

C41 Transfer of patent application or patent right or utility model
TR01 Transfer of patent right

Effective date of registration: 20040716

Address after: London, England

Patentee after: Albemarle chemicals UK Ltd

Address before: England

Patentee before: Rhodia Consumer Specialties Ltd.

C19 Lapse of patent right due to non-payment of the annual fee
CF01 Termination of patent right due to non-payment of annual fee